反应 #1253200

反应方程式

1 -(3,5 -Diamino-6-chloropyrazinoyl)-2-methyl-pseudothiourea hydroiodide

N-(benzyloxycarbonyloxy) succinimide

→

N-Cbz-1-(3,5-diamino-6-chloropyrazinoyl)-2-methyl-pseudothiourea

溶剂

DMF

DMF

triethylamine

反应条件

后处理

1. 1
   浓缩After this time, the reaction mixture was concentrated under reduced pressure
2. 2
   workup.ADDITIONSilica gel (25 g) was added to the solution
3. 3
   其他the solvent was evaporated
4. 4
   其他to leave the silica gel
5. 5
   其他was purified by flash chromatography on a FlashElute™ system from Elution Solution (P.O. Box 5147, Charlottesville, Va. 22905)

实验过程

1 -(3,5 -Diamino-6-chloropyrazinoyl)-2-methyl-pseudothiourea hydroiodide (II, 494 mg, 1.27 mmol) was dissolved in a mixture of anhydrous DMF(10 mL), and triethylamine (3 mL) followed by treatment with N-(benzyloxycarbonyloxy) succinimide (470 mg, 1.7 mmol) dissolved in DMF(3 mL). The reaction mixture was stirred overnight at room temperature. After this time, the reaction mixture was concentrated under reduced pressure and the residue suspended in ethyl acetate (30 mL). Silica gel (25 g) was added to the solution and the solvent was evaporated to leave the silica gel impregnated with the crude product that was purified by flash chromatography on a FlashElute™ system from Elution Solution (P.O. Box 5147, Charlottesville, Va. 22905) using a 90 g silica gel cartridge (eluent:hexanes, ethyl acetate=1:2). The purified N-Cbz-1-(3,5-diamino-6-chloropyrazinoyl)-2-methyl-pseudothiourea (III) was yield);1H NMR (360 MHz, DMSO-d6) δ2.33 (s, 3H), 2.61 (s, 3H), 4.99 (s, 2H), 7.39 (m, 10H), 13.7 (s, 1H); API MS m/z=395 [C15H15ClN6O3S+H]30; LC/MS (Method A)>99%, tr=10.1 min.

来源